Trails, Ales and Sails


Maine has long been know as vacationland. With thousands of miles of coastline, myriad mountains and forests Maine has drawn outdoor enthusiasts for hundreds of years.  In recent years, Maine has developed a reputation as a great state for beer. With 117 micro-breweries ranging from beer icons like Allagash to small one kettle operations, the beer scene in Maine offers something for everyone. Our week-long adventure is packed with fantastic activities and visits to some of Maine’s finest breweries.

  • Bike Along the Coast
  • Taste Great Craft Beer
  • Sail and Kayak
  • Enjoy Fresh Seafood

2022 Dates

June 12-17
September 18-23

Price $2895.00 pp



Pick Up/ Drop Off Map Depicting Several Coastal Maine Towns

Portland, Maine (PWM)

Day 1 Visiting Icons

Meet your guides early in the afternoon. No cycling today but the van will take us to some iconic breweries. First stop, Allagash Maines most recognized brewery. After a visit to the brewery and tasting room, we will visit one more brewery in the Industrial Way area before a 20- minute shuttle ride to Freeport for a visit to Maine Beer Company before a welcome dinner of fresh lobster overlooking the ocean.

Activity: none
Meals: Dinner
Lodging: The Regency Hotel

Day 2 Cycling the Eastern Trail

Today’s ride will feature the Eastern Trail which when completed will be a multi-use path from Maine to Florida. The ride will be a mix of on and off-road cycling featuring a ride through the Scarborough, Marsh. Our destination today is the town of Biddeford an old mill town featuring a charming downtown and a vibrant brewery scene. We will visit 3 breweries Banded Horn, Dirigo, and Barreled Souls before the van shuttles us back to Portland. Tonight enjoy a free night in Portland.

Activity: Cycling 20 or 30 miles
Meals: Breakfast and Lunch
Lodging: The Regency Hotel

Day 3 Explore the Water

Your day begins with a kayak adventure on Casco Bay. Paddle among the islands and Ft Gorgeous, the 19th-century fort standing guard in the heart of the bay. After kayaking, we take some time to explore Portland’s “Yeast Bayside” neighborhood that offers 6 breweries within easy walking distance of each other. In the evening enjoy a sunset sail on Casco Bay.

Activity: Sea kayaking and sailing
Meals: Breakfast, Lunch and, Dinner
Lodging: The Regency Hotel

Day 4 Cycling the Coast

The morning begins with a shuttle up the coast. We will get you on your bikes in the town of East Boothbay. Enjoy your ride along the coast before turning north and cycling to the town of Damariscotta you can explore the town before we visit Oxbow Brewing.

Activity: Cycling 17 miles
Meals: Breakfast and Dinner
Lodging: The Bradley Inn

Day 5 How Far would you go for a beer

An early morning ferry carries us to Monhegan Island 10 miles from the mainland. We enjoy a short hike to the backside of the island before we visit Monhegan Brewing. An afternoon ferry takes us further up the coast to our inn overlooking the ocean

Activity: Hiking 1 to 2 miles
Meals: Breakfast, Lunch, and Dinner
Lodging: The Craignair Inn

Day 6 Back to Portland

Enjoy an optional morning bike ride or choose to relax before a noon departure for Portland.

Activity: Cycling 20 miles
Meals: Breakfast

Browse Trips


  • Five nights’ lodging
  • All lodging taxes and gratuities
  • Most meals – including four dinners, five breakfasts, and four lunches
  • All taxes and gratuities for these meals
  • Hybrid Bike Rental
  • Expenses paid for ferry transits, kayaking, and sailing aboard the schooner
  • Tasting Fees at Breweries
  • Experienced Summer Feet Guides
  • Detailed route notes and maps
  • Van support including freshwater, ample snacks, and “relief rides”
  • Summer Feet Souvenirs – a cycling water bottle and t-shirt (available in men’s and women’s fit)


2020 Dates

June 14-19
September 13-18

Price $2895.00 pp

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